We should treat server-side software the same as client side software, and do incremental updates of our frameworks and languages – never more than one version behind. We should dedicate 20% of our time to upgrading and refactoring. Sure, they’ll be pain involved, but innovation stagnation due to old and tired software is far more detrimental than the short-term pain of upgrading.
Too true. We always stay close to the latest versions of underlying software (Ruby, Rails and a host of other plug-ins on our front-ends; Python, and a bunch of maths and language tools on our back-ends). Never more than one version behind